116-82-5

Basic information

• Product Name: 1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone
• Synonyms: sandoplastred2b;sumkaronred3b;ROSABOMIDE;1-amino-2-bromo-4-hydroxyanthracene-9,10-dione;1-azanyl-2-bromo-4-hydroxy-anthracene-9,10-dione;1-AMino-2-broMo-4-hydroxyanthrachinon;2-bromo-4-hydroxy- 1-Aminoanthraquinone;DISPERSE VIOLET 17
• CAS NO: 116-82-5
• Molecular Formula: C₁₄H₈BrNO₃
• Molecular Weight: 318.12
• EINECS: 204-160-4
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 116-82-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 232 °C(Solv: benzene (71-43-2))
• Boiling Point: 547.7 °C at 760 mmHg
• Flash Point: 285 °C
• Appearance: white powder
• Density: 1.6689 (rough estimate)
• Vapor Pressure: 1.32E-12mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• PKA: 6.41±0.20(Predicted)
• CAS DataBase Reference: 1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone(116-82-5)
• EPA Substance Registry System: 1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone(116-82-5)

Safety Data

• Hazardous Substances Data: 116-82-5(Hazardous Substances Data)

Usage

General Description

1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone is a chemical compound with the molecular formula C14H8BrNO3. It is a brominated derivative of anthraquinone, a polycyclic aromatic hydrocarbon. 1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone is used as a precursor in the synthesis of various organic compounds and dyes. Its bromine and hydroxyl groups make it useful for reactions involving nucleophilic substitution and oxidation. It is also known for its potential use as a photosensitizer in photodynamic therapy, a treatment for various diseases including cancer. Overall, 1-Amino-2-bromo-4-hydroxy-9,10-anthraquinone is a versatile compound with a wide range of potential applications in the field of organic chemistry and medical research.

InChI:InChI=1/C14H8BrNO3/c15-8-5-9(17)10-11(12(8)16)14(19)7-4-2-1-3-6(7)13(10)18/h1-5,17H,16H2

Synthetic route

4-hydroxy-1-aminoanthraquinone (116-85-8) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With bromine at 50 - 60℃; Bio-ionic liquid;	92%
With bromine; acetic acid
With bromine In nitrobenzene at 100 - 130℃; for 4h; Inert atmosphere;	33.9 g

1-amino-9,10-anthracenedione (82-45-1) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With bromine; boric acid In water	89.5%
With sulfuric acid; bromine; boric acid In ice-water
With sulfuric acid; bromine; boric acid; acetic acid In water

1-amino-2-bromo-4-phenoxy-9,10-antraquinone (102184-28-1) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With sulfuric acid; boric acid at 80 - 100℃; for 1.5h;	85%

3-bromo-5-hydroxyanthra<1,9-cd>isoxazol-6-one (82827-33-6) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With sulfuric acid at 100 - 110℃; for 0.25h;	74%

1-azido-4-bromoanthraquinone (74386-37-1) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With sulfuric acid at 60 - 70℃; for 0.5h;	71%

5-bromo-6-oxo-6H-anthra<1,9-cd>isoxazole (76924-08-8) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With sulfuric acid at 100 - 110℃; for 0.5h;	68%
With sulfuric acid at 110℃; Kinetics; various concentrations of H2SO4;

1-amino-2, 4-dibromoanthraquinone (81-49-2) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With sulfuric acid; boric acid
With sulfuric acid at 30 - 40℃;
With sulfuric acid at 100 - 110℃;

1-amino-4-methoxyanthraquinone (116-83-6) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With bromine; acetic acid

1-amino-2, 4-dibromoanthraquinone (81-49-2) + sulfuric acid (7664-93-9) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
at 100 - 110℃;
at 30 - 40℃;

3,5-dibromo-6-oxo-6H-anthra<1,9-cd>isoxazole (82840-40-2) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / dioxane / 0.5 h / 20 - 25 °C 2: 80 percent / H2 / 0.2percent Pd/C / ethanol / 24 h / 40 - 50 °C / 760 Torr 3: 85 percent / 80percent H2SO4, H3BO3 / 1.5 h / 80 - 100 °C View Scheme

3-bromo-5-phenoxy-6-oxo-6H-anthra<1,9-cd>isoxazole (106960-84-3) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / H2 / 0.2percent Pd/C / ethanol / 24 h / 40 - 50 °C / 760 Torr 2: 85 percent / 80percent H2SO4, H3BO3 / 1.5 h / 80 - 100 °C View Scheme

1-azido-2-bromo-4-hydroxyanthraquinone (82827-32-5) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / acetic acid / 0.67 h / Heating 2: 74 percent / 90percent H2SO4 / 0.25 h / 100 - 110 °C View Scheme

sulfuric acid monohydrate (50981-12-9, 10193-30-3) + 1-amino-2, 4-dibromoanthraquinone (81-49-2) → 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5)

Conditions	Yield
With nitrogen; paraformaldehyde In water

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + phenol (108-95-2) → C. I. disperse red 60 (17418-58-5)

Conditions	Yield
With pyridine; sodium carbonate at 150 - 155℃; for 9h; Reagent/catalyst; Sealed tube; Large scale;	99%
With potassium hydroxide In water; N,N-dimethyl-formamide at 120 - 125℃; for 3h;

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + methyl iodide (74-88-4) → 1-amino-2-bromo-4-methoxyanthracene-9,10-dione (159389-46-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 14h;	96%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 1-ethynyl-2,3,5,6-tetramethylbenzene (134307-04-3) → 1-amino-4-hydroxy-2-[(2,3,5,6-tetramethylphenyl)ethynyl]-9,10-anthraquinone (1450664-35-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In toluene at 75℃; for 1h; Inert atmosphere;	94%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + trimethylsilylacetylene (1066-54-2) → 1-amino-4-hydroxy-2-[(trimethylsilyl)ethynyl]-9,10-anthraquinone (1260379-10-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In toluene at 43℃; for 10h; Inert atmosphere;	88%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 4-ethynyl-4a,5-dihydroisoquinoline (78593-42-7) → 1-amino-4-hydroxy-2-[(isoquinolin-4-yl)ethynyl]-9,10-anthraquinone (1450664-34-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In toluene at 65℃; for 12h; Inert atmosphere;	85%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + tert-octylphenol (140-66-9) → 1-amino-4-hydroxy-2-[4-(1,1,3,3-tetramethyl-butyl)-phenoxy]anthraquinone

Conditions	Yield
With potassium carbonate at 150℃; for 15h;	84%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) → 1-azido-2-bromo-4-hydroxyanthraquinone (82827-32-5)

Conditions	Yield
	78%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 4-methoxyphenylacetylen (768-60-5) → 1-amino-4-hydroxy-2-[(4-methoxyphenyl)ethynyl]anthracene-9,10-dione (1338810-36-8)

Conditions	Yield
With pyridine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 75℃; for 6h; Sonogashira coupling; Inert atmosphere;	76%

4-bromo-1-ethynylbenzene (766-96-1) + 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) → 1-amino-2-[(4-bromophenyl)ethynyl]-4-hydroxyanthracene-9,10-dione (1338810-35-7)

Conditions	Yield
With pyridine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 70℃; for 4h; Sonogashira coupling; Inert atmosphere;	72%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + phenylacetylene (536-74-3) → 1-amino-4-hydroxy-2-(phenylethynyl)anthracene-9,10-dione (1338810-33-5)

Conditions	Yield
With pyridine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 45℃; for 11h; Sonogashira coupling; Inert atmosphere;	72%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + (1,5-dimethyl-4-pyrazolyl)acetylene (61514-54-3) → 1-amino-2-[(1,5-dimethyl-1H-pyrazol-4-yl)ethynyl]-4-hydroxyanthracene-9,10-dione (1338810-37-9)

Conditions	Yield
With pyridine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 75℃; for 8h; Sonogashira coupling; Inert atmosphere;	70%

(4-Nitrophenyl)acetylene (937-31-5) + 1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) → 1-amino-4-hydroxy-2-[(4-nitrophenyl)ethynyl]anthracene-9,10-dione (1338810-34-6)

Conditions	Yield
With pyridine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 70℃; for 3h; Sonogashira coupling; Inert atmosphere;	64%

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) → 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid (24929-02-0)

Conditions	Yield
With water; sodium sulfite

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) → 8,17-dihydroxy-6,15-dihydro-dinaphtho[2,3-a;2',3'-h]phenazine-5,9,14,18-tetraone (6871-71-2)

Conditions	Yield
With sodium hydroxide; naphthalene; copper at 210 - 220℃;
With sodium acetate; copper; nitrobenzene at 210℃;

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 2,5-furandicarbonyl dichloride (10375-34-5) → furan-2,5-dicarboxylic acid bis-(2-bromo-4-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthrylamide)

Conditions	Yield
With nitrobenzene at 160℃;

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + acetic anhydride (108-24-7) → 1-acetylamino-2-bromo-4-hydroxy-anthraquinone

Conditions	Yield
With sodium acetate

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + para-thiocresol (106-45-6) → 1-amino-4-hydroxy-2-p-tolylsulfanyl-anthraquinone (79609-80-6)

Conditions	Yield
With potassium hydroxide

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 4-acetamido-2-methylphenol (16375-90-9) → N-[4-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-3-methyl-phenyl]-acetamide (38920-11-5)

Conditions	Yield
(i) K2CO3, (ii) /BRN= 1887275/; Multistep reaction;

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 2-chloro-5-acetylamino phenol (28443-52-9) → N-[3-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-4-chloro-phenyl]-acetamide (38912-95-7)

Conditions	Yield
(i) K2CO3, Py, (ii) /BRN= 1887275/; Multistep reaction;

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 1-(3-hydroxyphenyl)-3-phenylurea (13142-80-8) → 1-[3-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-phenyl]-3-phenyl-urea (38924-13-9)

Conditions	Yield
(i) K2CO3, Py, (ii) /BRN= 1887275/; Multistep reaction;

1-amino-2-bromo-4-hydroxyanthraquinone (116-82-5) + 4-acetaminophenol (103-90-2) → N-[4-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-phenyl]-acetamide (38919-98-1)

Conditions	Yield
(i) K2CO3, (ii) /BRN= 1887275/; Multistep reaction;

Upstream product

• 102184-28-1 1-amino-2-bromo-4-phenoxy-9,10-antraquinone 
• 81-49-2 1-amino-2, 4-dibromoanthraquinone 
• 7664-93-9 sulfuric acid 
• 82-45-1 1-amino-9,10-anthracenedione 
• 50981-12-9 sulfuric acid monohydrate 
• 82827-32-5 1-azido-2-bromo-4-hydroxyanthraquinone 
• 106960-84-3 3-bromo-5-phenoxy-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 82840-40-2 3,5-dibromo-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 74386-37-1 1-azido-4-bromoanthraquinone 
• 82827-33-6 3-bromo-5-hydroxyanthra<1,9-cd>isoxazol-6-one 
• 76924-08-8 5-bromo-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 116-83-6 1-amino-4-methoxyanthraquinone 
• 116-85-8 4-hydroxy-1-aminoanthraquinone 

Downstream Products

• 24929-02-0 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid 
• 6871-71-2 8,17-dihydroxy-6,15-dihydro-dinaphtho[2,3-a;2',3'-h]phenazine-5,9,14,18-tetraone 
• 1450664-35-3 1-amino-4-hydroxy-2-[(2,3,5,6-tetramethylphenyl)ethynyl]-9,10-anthraquinone 
• 1450664-38-6 4-acetoxy-1-amino-2-[(2,3,5,6-tetramethylphenyl)ethynyl]-9,10-anthraquinone 
• 1450664-33-1 5-hydroxy-3-(2,3,5,6-tetramethylbenzoyl)-1H-naphtho[2,3-g]indazole-6,11-dione 
• 1338810-36-8 1-amino-4-hydroxy-2-[(4-methoxyphenyl)ethynyl]anthracene-9,10-dione 
• 1338810-33-5 1-amino-4-hydroxy-2-(phenylethynyl)anthracene-9,10-dione 
• 1338810-48-2 3-[(4-bromophenyl)ethynyl]-5-hydroxy-6H-anthra[1,9-cd]isoxazol-6-one 
• 1338810-47-1 3-[(4-nitrophenyl)ethynyl]-5-hydroxy-6H-anthra[1,9-cd]isoxazol-6-one 
• 1338810-46-0 5-hydroxy-3-(phenylethynyl)-6H-anthra[1,9-cd]isoxazol-6-one 
• 1338810-49-3 3-(4-methoxybenzoyl)-6,11-dioxo-6,11-dihydro-1H-naphtho[2,3-g]indazol-5-yl acetate 
• 1338810-45-9 1-azido-2-[(4-bromophenyl)ethynyl]-4-hydroxyanthracene-9,10-dione 
• 1338810-44-8 1-azido-4-hydroxy-2-[(4-nitrophenyl)ethynyl]anthracene-9,10-dione 
• 1338810-43-7 1-azido-4-hydroxy-2-(phenylethynyl)anthracene-9,10-dione 

Relevant articles and documents

Halogenation reactions in biodegradable solvent: Efficient bromination of substituted 1-aminoanthra-9,10-quinone in deep eutectic solvent (choline chloride:urea)

A simple ammonium deep eutectic solvent was used as a dual catalyst and environmentally benign reaction medium for the bromination of 1-aminoanthra-9,10-quinone, eliminating the need for volatile organic solvents and concentrated acids like H2SO4 as solvents or catalysts. This simple ammonium deep eutectic solvent, easily synthesized from choline chloride and urea, is relatively inexpensive and biodegradable, making it applicable for industrial applications. The deep eutectic solvent was easily separated and reused without loss of activity, and thus provides a good alternative for industrial bromination of 1-aminoanthra-9,10-quinone.

CHARACTERISTICS OF THE ALKOXYLATION OF HALOGENO-6-OXO-6H-ANTHRAISOXAZOLES

The alkylation of 6-oxo-6H-anthraisoxazoles containing a chlorine or bromine atom at position 3 and also a bromine at position 5 takes place with substitution of the halogen or hydrogen, depending on the structure of the alkoxide ion and the type of halogen.

Process for the preparation of a mixture of 1-amino-2-chloro-4-hydroxyanthraquinone and 1-amino-2-bromo-4-hydroxyanthraquinone

A process for the preparation of a mixture of 1-amino-2-chloro-4-hydroxyanthraquinone and 1-amino-2-bromo-4-hydroxyanthraquinone, which mixture contains a high proportion of 1-amino-2-chloro-4-hydroxyanthraquinone, by chlorinating and brominating 1-aminoanthraquinone and reacting the intermediate so obtained with concentrated or fuming sulfuric acid.